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Enantioselective Syntheses of syn- and anti-β-Hydroxyallylsilanes Via Allene Hydroboration-Aldehyde Allylboration Reactions

Year: 2011

Type: article

Abstract: The kinetic hydroboration of allenylsilane 5 with ((d)Ipc)(2)BH at -40 °C provides allylborane 9Z with ≥12:1 selectivity. When the hydroboration is performed at temperatures above -40 °C, 9Z isomerizes to the thermodynamically more stable allylborane 9E with >20:1 selectivity. Subsequent treatment of 9Z or 9E with aldehydes at -78 °C provides syn- or anti-β-hydroxyallylsilanes, 7 or 8, respectively.

Source: Organic Letters

DOI: 10.1021/ol200392u

Authors: Ming Chen, William R. Roush

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Acyclic Diastereoselection: Methodology and Synthesis, G918211471

OpenAlex ID: W1970853752

FWCI: 3.462

Cites: 74

Cited by: 39

Related to: 10